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Details

Stereochemistry ACHIRAL
Molecular Formula C11H14N2O4
Molecular Weight 238.2399
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FELBAMATE

SMILES

NC(=O)OCC(COC(N)=O)C1=CC=CC=C1

InChI

InChIKey=WKGXYQFOCVYPAC-UHFFFAOYSA-N
InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

HIDE SMILES / InChI

Description

Felbamate is an antiepileptic indicated as monotherapy or as an adjunct to other anticonvulsants for the treatment of partial seizures resulting from epilepsy. Receptor-binding studies in vitro indicate that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding, and is devoid of activity at the MK-801 receptor binding site of the NMDA receptor-ionophore complex. However, felbamate does interact as an antagonist at the strychnine-insensitive glycine recognition site of the NMDA receptor-ionophore complex. The mechanism by which felbamate exerts its anticonvulsant activity is unknown, but in animal test systems designed to detect anticonvulsant activity, felbamate has properties in common with other marketed anticonvulsants. In vitro receptor binding studies suggest that felbamate may be an antagonist at the strychnine-insensitive glycine-recognition site of the N-methyl-D-aspartate (NMDA) receptor-ionophore complex. Antagonism of the NMDA receptor glycine binding site may block the effects of the excitatory amino acids and suppress seizure activity. Animal studies indicate that felbamate may increase the seizure threshold and may decrease seizure spread. It is also indicated that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding. Felbamate should be used only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use. Felbatol is the brand name used in the United States for felbamate.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.52 mM [IC50]
2.02 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FELBATOL

Cmax

ValueDoseCo-administeredAnalytePopulation
49 μg/mL
45 mg/kg 1 times / day steady-state, oral
FELBAMATE plasma
Homo sapiens
14.2 μg/mL
1200 mg single, oral
FELBAMATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
526 μg × h/mL
1200 mg single, oral
FELBAMATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
45 mg/kg 1 times / day steady-state, oral
FELBAMATE plasma
Homo sapiens
19.2 h
1200 mg single, oral
FELBAMATE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Adjunctive therapy: 1200 mg/day in 3-4 divided doses. The daily dose can be increased in 1200 mg increments each week as tolerated to response. Maximum daily dose: 3600 mg. Monotherapy: 1200 mg/day in 3-4 divided doses. Increase the daily dose in 600 mg increments every two weeks as tolerated to response.
Route of Administration: Oral
In Vitro Use Guide
At concentrations of 30 to 100 nM, Felbamate produced a significant inhibition of high-voltage-activated Ca++ currents (-6/-15%). At saturating concentrations (1-3 uM), Felbamate-mediated inhibition averaged 44% in rat cortical and neostriatal neurons.